Tuscany's – A Symphony of Vines, Villages, and Velvet Sunsets
October 8th to 15th, 2027
Trip Overview Join us in the heart of Tuscany for an unforgettable 8-day adventure from October 8th to October 15th, 2027! This trip is crafted to blend relaxation with exhilarating days exploring Tuscany’s rolling hills, medieval villages, and world-class wineries. Our home base is a stunning villa in Montefollonico, offering private suites with breathtaking views of the Tuscan countryside and Montepulciano. With a private chef preparing daily breakfasts, luxurious dinners at Tuscany’s finest restaurants, and a “leave your wallet at home” approach, every detail is designed for ease and indulgence. Expect ample walking opportunities, an exciting e-bike tour, and a day driving vintage Fiats for a truly unique experience. The group size is 16 people, consisting of 14 guests plus your hosts.
Highlights
Luxurious Villa Stay: Settle into a private suite at our Montefollonico villa with panoramic views, a pool, and personalized comfort.
Culinary Delights: Savor multi-course dinners at iconic restaurants like Ristorante Daria and Osteria Acquacheta, plus a hands-on Tuscan cooking class.
Wine Tastings: Visit legendary wineries like Contucci, Baracchi, and Cantine Innocenti for exclusive tours and tastings.
Adventure & Exploration: Drive vintage Fiats through the countryside, hunt for truffles, and walk through Tuscany’s lush hills.
Cultural Immersion: Wander medieval Montepulciano, Cortona, and Pienza, with optional guided tours and free time to explore.
Day 1: October 8, 2027 – Arrival in Montefollonico Our journey begins in Florence, where a private shuttle picks you up from your chosen location (airport or hotel) for a scenic 1.5-hour drive to our Montefollonico villa. Nestled on a sprawling estate with views of Montepulciano, this beloved villa offers private suites with dedicated bathrooms and customizable climate control. Upon arrival, enjoy a warm welcome reception, followed by a multi-course Tuscan dinner, prepared by our private chef team and paired with local wines. Accommodation: Montefollonico Villa
Day 2: October 9, 2027 – Montepulciano & Contucci Winery Start with a chef-prepared breakfast at the villa. We’ll drive 15 minutes to Montepulciano for a wine tasting at Contucci Winery, led by 41st-generation owner Andrea Contucci. Savor their world-renowned vintages in the heart of the town square. Enjoy a scenic lunch at Ristorante Romantico, followed by free time to explore Montepulciano’s medieval streets, shops, and gelato spots. Return to the villa for poolside relaxation or a glass of wine. We’ll head to Ristorante Daria in Monticchiello for dinner in a charming medieval village setting. Accommodation: Montefollonico Villa
Day 3: October 10, 2027 – Truffle Hunting & Podere Il Casale After breakfast, depart for Podere Il Casale. Embark on a truffle-hunting adventure with a local guide and trained dogs, digging for treasures in a nearby forest. Enjoy a 5-hour experience with an outdoor lunch on a terrace overlooking Tuscany’s hills, featuring your freshly found truffles paired with local wines. Return to the villa for free time to relax by the pool or nap. Head to Idyllium in Pienza for dinner on a breathtaking terrace with Val d’Orcia views, known for its exceptional food and wine pairings. Accommodation: Montefollonico Villa
Day 4: October 11, 2027 – E-Bike Adventure Enjoy breakfast before departing to Montepulciano’s Urban Bikery. Embark on a 5-hour guided e-bike tour through Tuscany’s rolling hills, with a support van and stops at a countryside farmhouse for lunch. Savor gelato at Buongusto Gelateria Montepulciano, then return to the villa. Head to Osteria Acquacheta in Montepulciano for dinner, famous for its open-kitchen grilling and vibrant atmosphere. Accommodation: Montefollonico Villa
Day 5: October 12, 2027 – Baracchi Winery & Cortona After breakfast, depart for Baracchi Winery, a 5th-generation estate known for its Michelin-starred restaurant. Enjoy a winery tour, tasting, and iconic lunch. Head to Cortona for an optional guided tour or free exploration of this charming hilltop town. Stop for gelato at Dolce Vita before returning to the villa. Dine at Ristorante La Chiusa, a historic estate with Etruscan roots, offering a magical dining experience steeped in history. Accommodation: Montefollonico Villa
Day 6: October 13, 2027 – Spa Day & Cantine Innocenti Enjoy breakfast, then depart for a 5-hour wellness day at Spa Terme Sensoriali, featuring saunas, steam rooms, pools, mud baths, and massages. Lunch is included at the spa. Head to Cantine Innocenti in Montefollonico for a wine tasting at this family-run winery, known for its romantic, small-scale charm. Walk 5 minutes to 13 Gobbi for an authentic Tuscan dinner in Montefollonico’s quiet, medieval village. Accommodation: Montefollonico Villa
Day 7: October 14, 2027 – Vintage Fiat Adventure & Cooking Class After breakfast, depart for a thrilling day driving vintage Fiats through Tuscany’s countryside, guided by the rental company. This guest-favorite experience lasts until afternoon, followed by a return to the villa for relaxation. Join our villa’s chef team for a hands-on Tuscan cooking class, followed by a final dinner featuring your creations, paired with local wines. Accommodation: Montefollonico Villa
Day 8: October 15, 2027 – Departure Enjoy a final breakfast before departing the villa for Florence, with drop-off at your chosen location (airport or hotel). Reflect on a week of Tuscan magic—vineyards, villages, and unforgettable moments with new friends.
What’s Included
7 nights in a private suite at our Montefollonico villa
All meals, snacks, drinks and all else you’d like
All activities, winery tours, and tastings
Private transportation throughout the trip
E-bike tour, vintage Fiat rentals, and spa day
24/7 support from your hosts
What’s Not Included
Airfare to/from Florence
Personal expenses
Travel insurance (highly recommended)
Why Book This Trip? This Tuscany adventure offers a perfect balance of luxury, adventure, and relaxation, with a single villa base eliminating the hassle of packing and unpacking. From truffle hunting to driving vintage Fiats, every day brings new delights, complemented by world-class wines, exquisite meals, and the charm of Tuscany’s medieval villages. With your hosts, you’ll enjoy a seamless, immersive experience in one of Italy’s most iconic regions. Ready to Book?
